This is a spinoff to @stargal's overrated companies question. Are there any luxury brands that you think are worth the price tag? Are there any that you would buy if you could afford it?
In general I like to think that I am a pretty reasonable shopper, but I will definitely spend a little bit more on shoes if they are comfortable and fit me well. I have a couple of pairs of Tory Burch flats and a pair of Frye boots. My disclaimer is that I bought them all on a pretty good sale, but they were still ten times more what I normally pay. Still worth it to me since they are the three shoes I wear the most over the course of the whole year.